The series sounds like it could be really great, I wonder if they have a frequency for new interviews planned already? The series title alone got me though, as someone who is working on a startup that is something I really aspire to be, profitable and proud.
Campaign Monitor is a great service too, I frequently reference and share their Guide to CSS support http://www.campaignmonitor.com/css/ to coworkers who have questions on what can and can't be done with styling in emails.
We have a couple of other companies lined up but there's no schedule yet. Hopefully we'll start getting a steady flow of suggestions for companies that fit the profile and do something every couple of weeks.
This looks like it could be pretty interesting. 37signals feels like something of an outlier to me: they talk a good game, but I don't really get the feeling that I could do something similar, because I don't have a hugely popular blog, nor did I create an extremely popular web framework.
Plenty, but it's a lot easier for a company to bootstrap and hit $1MM in revenues and be profitable than it is to be the next Apple or Google or younameit.
Hitting $1MM in revenues strikes me as "about as difficult" as raising a series A if not harder. However, having to bootstrap places constraints on the type of product/company one can build. There is also the time factor. Some products have a right time and place and bootstrapping may lead to missing a window of opportunity.
Trying to be the next google or younameit is playing the lottery, no argument there. Bootstrapping to $10-100MM strikes me about as unlikely as being the next google.
Is there anything stopping you from creating a modestly successful blog or a piece of OSS which solves a big problem in an underserved niche for very gabby programmers?
with tools like Amazon Web services, Basecamp, Github, Chargify, and loads of other building blocks, do you realize how easy it is for a single individual to take an idea to concept to large service quickly?
This 37Signals post, and subsequent ones, should inspire you, not discourage you.
The problem isn't so much the building-something as the building-something-popular, though. Since, as you point out, it's easy for a single individual to build large services these days, many thousands of single individuals are doing just that, so there's a lot of competition for attention/users/readers/etc.
Campaign Monitor is a great service too, I frequently reference and share their Guide to CSS support http://www.campaignmonitor.com/css/ to coworkers who have questions on what can and can't be done with styling in emails.